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5-Nitrovanillin

5-Nitrovanillin structure

CAS No:
6635-20-7
Formula:
C8H7NO5
Chemical Name:
5-Nitrovanillin
Synonyms:
Benzaldehyde,4-hydroxy-3-methoxy-5-nitro-;Vanillin,5-nitro-;4-Hydroxy-3-methoxy-5-nitrobenzaldehyde;5-Nitrovanillin;3-Methoxy-4-hydroxy-5-nitrobenzaldehyde;5-Nitro-4-hydroxy-3-methoxybenzaldehyde;4-Hydroxy-5-methoxy-3-nitrobenzaldehyde;3-Nitro-4-hydroxy-5-methoxybenzaldehyde;NSC 16932;NSC 35352
Categories:
Chemical Reagents > Organic Reagents

Description

yellow-green fine crystalline powder

5-nitrovanillin is a member of the class of benzaldehydes that is vanillin in which the hydrogen ortho- to the hydroxy group is substituted by a nitro group. It is a member of benzaldehydes and a member of 2-nitrophenols. It derives from a vanillin.

5-Nitrovanillin Basic Attributes

Molecular Weight：

197.14

Exact Mass：

197.14

BRN：

1973746

EC Number：

229-633-2

UNII：

G6SQ47R9WB

NSC Number：

35352|16932

DSSTox ID：

DTXSID2075344

HScode：

29130000

Characteristics

PSA：

92.4

XLogP3：

1.4

Appearance：

Yellow to green powder.

Density：

1.5±0.1 g/cm3

Melting Point：

175-176 °C

Boiling Point：

320.9°C at 760 mmHg

Flash Point：

97℃

Refractive Index：

1.629

Storage Conditions：

Store below +30°C.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36-24/25

Marks：

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

5-Nitrovanillin Use and Manufacturing

Phenol (94 mg, 1 mmol) dissolved in 3 mL glacial acetic acidin a 50 mL test tube was treated with solid Y(NO3)3.6H2O(383 mg, 1 mmol) with constant shaking at RT for 10 min.The reaction was monitored by TLC at 10percent EtOAc inPetroleum benzene. Ice-cold water (30 mL) was added to thereaction mixture after completion of reaction and left for 15min. Solid was collected by filtration and washed with water.Solid product isolated in this way was used for analysis withoutfurther purification. Experimental procedure for the synthesisof compounds 2a–2e is mentioned in the SupportingInformation.To a solution of vanillin (5.0 g, 32.9 mmol) in acetic acid (50 ml) was added nitric acid (60percent, 2.6 ml) slowly at 0 °C. Afterwards the solution was warmed up to room temperature and allowed to stir for another 30 min. The precipitate was filtered off and washed with cold water, to give compound 94 as a yellow solid (5.40 g, 83percent). 120 ml of chloroform, 15.2 g of vanillin and 2.8 g of SAPO-11 molecular sieve catalyst were uniformly stirred, 4.0 ml of nitrogen dioxide was added, and the mixture was stirred in an oxygen atmosphere and reacted at 10° C. for 12 h. After the reaction was completed, the mixture was filtered to separate SAPO-. 11 Catalyst, the organic phase was washed several times with distilled water to neutrality and distilled under reduced pressure to give 15.52 g of 5-nitro vanillin in a yield of 78.8percent.To a solution of vanillin (7) (10 g, 65 mmol) in acetic acid stirred at 5 °C under nitrogen atmosphere, nitric acid (70 percent) was added carefully over a period of 30 minutes. The yellow coloured solid formed was filtered washed with water throughly to wash out acetic acid and allowed to dry under vaccum to afford 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (9) as yellow solid (9.5 g, 74 percent); mp: 171The 5-nitrovanillin compound was synthesized fromVanillin by Yadav method [10] with some modifications. Avanillin (0.07 mol) was dissolved in 55 mL of dichloromethane, squirted by 12 mL of HNO3, then stirred for 20 min at roomtemperature, added 25 mL of ice water then leave it for 2 h, the solid formed was recrystallized with ethanol. The meltingpoint of synthesized product was determined and characterizedby FTIR instrument. The synthesized 5-nitrovanillin is lightyellow powder, 64 percent yield, m.p 175-177 °C (reference, 176°C); FTIR (KBr, νmax, cm–1): 1560.77 due to NO2 group

Computed Properties

Molecular Weight:197.14
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:197.03242232
Monoisotopic Mass:197.03242232
Topological Polar Surface Area:92.4
Heavy Atom Count:14
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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