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Home > Encyclopedia > Benzyl chloroformate

Benzyl chloroformate

Benzyl chloroformate structure

Benzyl chloroformate 

structure
  • CAS No:

    501-53-1

  • Formula:

    C8H7ClO2

  • Chemical Name:

    Benzyl chloroformate

  • Synonyms:

    Carbonochloridic acid,phenylmethyl ester;Formic acid,chloro-,benzyl ester;Benzyl chloroformate;(Benzyloxy)carbonyl chloride;Carbobenzoxy chloride;Carbobenzyloxy chloride;Chloroformic acid benzyl ester;Benzyl carbonochloridate;Benzyl chlorocarbonate;Phenylmethyl chloroformate;NSC 83466;Benzyl chloridocarbonate;Benzyloxyformyl chloride;94274-21-2;728010-31-9;960053-05-8

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

light yellow liquid


Benzyl chloroformate appears as a colorless liquid with an acrid odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Long-term inhalation of low concentrations or short-term inhalation of high concentrations can result in adverse health effects.|Liquid|OILY COLOURLESS-TO-YELLOW LIQUID WITH PUNGENT ODOUR.


Benzyl chloroformate appears as a colorless liquid with an acrid odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Long-term inhalation of low concentrations or short-term inhalation of high concentrations can result in adverse health effects.

Benzyl chloroformate Basic Attributes

170.59

170.59

207-925-0

170BP0DD31

0990

83466

1739

DTXSID9027158

OILY LIQUID|COLORLESS TO PALE YELLOW LIQUID

2915900090

Characteristics

26.3

2.68

Clear slightly yellow to slightly pink Solution

1.2166 g/cm3 @ Temp: 20 °C

-20 °C

152 °C @ Press: 760 Torr

197 °F

1.531

Decomposes in water.Miscible with ether, acetone and benzene.

2-8°C

1.39 psi ( 20 °C)

1 (vs air)

Oral-Rat LD50: 3000 mg/kg; Inhalation-Rat LC50: 590 mg/m3/4 hours

Decomposes carbon dioxide and toxic chlorides and phosgene vapors when exposed to heat; emits toxic and corrosive hydrogen chloride gas when exposed to water

CONTAINERS MAY EXPLODE /DURING FIRE/.

ACRID ODOR

DECOMP TO CO2 & BENZYL CHLORIDE UPON HEATING AT 100-155 °C|DECOMP IN HOT ETHANOL & WATER|CONVERSION FACTORS: 6.96 MG/CU M= 1 PPM|Reacts with water to form hydrochloric acid|Flash point: 80.0 °C (Tag open cup), 107.9 °C (Tag closed cup)

Decomposes in moist air. Decomposes slowly in water to give corrosive hydrochloric acid and organic acids.

Acyl Halides, Sulfonyl Halides, and Chloroformates

Water-Reactive

BENZYL CHLOROFORMATE decomposes slowly in water forming benzyl alcohol, HCl, and CO2. Gives off HCl fumes in moist air. Reacts with bases, both organic and inorganic. Attacks many metals especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. Catalytic impurity incidents involving the iron catalyzed decomposition of benzoyl chloroformate have caused several explosions. The iron presumably comes from corrosion of steel storage tanks [Loss Prev. Bull., 1975, (003), 2]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

-10.000 BTU/LB= -5,700 CALORIES/G= -240X10+5 JOULES/KG (ESTIMATED)

Corrosive

90 BTU/LB= 50 CALORIES/G= 2.1X10+5 JOULES/KG (ESTIMATED)

Safety Information

I

8

UN 2924 3/PG 2

3

45-20-34-48/22-50/53-67-65-63-48/20-11-43-37-23

53-26-36/37/39-45-60-61-62-46-36/37

LQ5860000

T,C,N,F

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and alkalis

Under the catalysis of iron salt, it decomposes and explodes violently; It is strongly corrosive and irritating; Thermally unstable

Stable. Incompatible with water, oxidizing agents. Combustible.

P201-P261-P273-P280-P305 + P351 + P338-P310

H314-H335-H350-H410

FORMS HYDROGEN CHLORIDE (HYDROCHLORIC ACID) WITH WATER; REACTION IS VERY VIGOROUS IN COLD WATER|DANGEROUS ... WILL REACT WITH WATER OR STEAM TO PRODUCE HEAT, TOXIC AND CORROSIVE FUMES.|The ester is made by adding benzyl alcohol slowly to a preformed solution of phosgene in toluene at 12-16 °C, toluene solvent finally being distilled off under vacuum. When discolored phosgene was used (probably containing iron salts from corrosion of the cylinder), a violent explosion occurred during the distillation phase, presumably involving iron-catalysed decomposition of the chloroformate ester.

Special Hazards of Combustion Products: Toxic phosgene, hydrogen chloride, and benzyl chloride vapors may form. Behavior in Fire: Containers may explode. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.|Corrosives, Flammable - 2nd degree

|Danger|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, and P501|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P271, P273, P280, P284, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 154 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H227: Combustible liquid [Warning Flammable liquids]|P210, P280, P370+P378, P403+P235, and P501

Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Use water spray to reduce vapors; do not put water directly on leak, spill area or inside container. Keep combustibles (wood, paper, oil, etc.) away from spilled material. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Self-contained breathing apparatus or acid-type canister mask; goggles or face shield; rubber gloves; protective clothing. (USCG, 1999)|SELF-CONTAINED BREATHING APPARATUS OR ACID-TYPE CANISTER MASK; GOGGLES OR FACE SHIELD; RUBBER GLOVES; PROTECTIVE CLOTHING.

COMBUSTIBLE

CONTAINERS MAY EXPLODE /DURING FIRE/.

EXTINGUISH WITH DRY CHEMICALS, FOAM OR CARBON DIOXIDE.|If material on fire or involved in fire: Use dry chemical, dry sand, or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.|Personnel protection: Avoid breathing vapors. Keep upwind. Wear positive pressure self-contained breathing apparatus. Avoid bodily contact with the material. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.

/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Fire or Explosion: EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.|/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Health: CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.|/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for BENZYL CHLOROFORMATE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

INHALATION CAUSES MUCOUS MEMBRANE IRRITATION. EYES ARE IRRITATED BY EXCESSIVE EXPOSURE TO VAPOR. LIQ CAUSES IRRITATION OF EYES & IRRITATES SKIN.

Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: complete protective clothing including self-contained breathing apparatus.

Separated from food and feedstuffs. Dry. Well closed.

A harmful concentration of airborne particles can be reached quickly on spraying.

Lachrymation. The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the aerosol may cause lung oedema. The effects may be delayed. Medical observation is indicated.

NO open flames. NO contact with water.

AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

moderately toxic

Drug Information

May contain 3% or less benzyl chloride

Inhalation causes mucous membrane irritation. Eyes are irritated by excessive exposure to vapor. Liquid causes severe irritation of eyes and irritates skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

INHALATION: remove from exposure; support respiration; call physician. EYES: irrigate with copious amounts of water for 15 min. SKIN: flush with large quantities of water; wash with soap and water. INGESTION: give large amounts of water; do NOT induce vomiting. (USCG, 1999)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

... LACRIMATOR.|INHALATION CAUSES MUCOUS MEMBRANE IRRITATION. EYES ARE IRRITATED BY EXCESSIVE EXPOSURE TO VAPOR. LIQ CAUSES IRRITATION OF EYES & IRRITATES SKIN. INGESTION CAUSES IRRITATION OF MOUTH & STOMACH.

benzyl chloroformate

The substance can be absorbed into the body by inhalation and by ingestion.

Cough. Shortness of breath. Sore throat. Laboured breathing.


Skin burns.


Watering of the eyes. Severe deep burns.

Benzyl chloroformate Use and Manufacturing

Methods of Manufacturing

/IT IS PREPARED/ ... BY ACTION OF PHOSGENE ABSORBED IN TOLUENE ON BENZYL ALCOHOL: CARTER ET AL, ORG SYN 23, 13 (1943); BY REACTING CARBONYL CHLORIDE & BENZYL ALCOHOL @ -20 TO -30 °C

Uses

In peptide synthesis to block the amino group.


Intermediates


Used as a chemical intermediate.

Production

500,000 - 1,000,000 lb

APPROX 100% AS A REAGENT IN /PRC: ORGANIC/ SYNTHESIS

GRADE OR PURITY: 97+%|Typical specifications of commercial chloroformates: purity, 98%; phosgene, <0.1%, iron, <10 ppm; acidity as HCl, <0.1%; alcohol or phenol, <2% /Chloroformic esters/|Commercial products have concentrations of 97-99 wt% /Chloroformic esters/|97%; 50 wt% in toluene

All other basic organic chemical manufacturing|Carbonochloridic acid, phenylmethyl ester: ACTIVE|Most chloroformate production is used captively and production figures are not available /Chloroformic esters/

Fire Hazards -> Corrosives, Flammable - 2nd degree

Computed Properties

Molecular Weight:170.59
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:170.0134572
Monoisotopic Mass:170.0134572
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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