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Methyl carbazate

Methyl carbazate structure

CAS No:
6294-89-9
Formula:
C2H6N2O2
Chemical Name:
Methyl carbazate
Synonyms:
Hydrazinecarboxylic acid,methyl ester;Carbazic acid,methyl ester;Methyl carbazate;Methyl hydrazinoformate;Methyl hydrazinocarboxylate;Carbomethoxyhydrazide;(Methoxycarbonyl)hydrazine;Methyl hydrazinecarboxylate;Methyl carbazinate;(Methoxycarbonyl)hydrazide;Carbomethoxyhydrazine;NSC 11709;N-(Methoxycarbonyl)hydrazine
Categories:
Pharmaceutical Intermediates > Antiemetics

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Description

WHITE TO PINK CRYSTALLINE PLATELETS

Methyl carbazate Basic Attributes

Molecular Weight：

90.08

Exact Mass：

90.08

BRN：

1679395

EC Number：

228-560-3

UNII：

0L5442J16Q

NSC Number：

11709

DSSTox ID：

DTXSID3020835

HScode：

2928000090

Characteristics

PSA：

64.4

XLogP3：

-0.8

Appearance：

White to pink Crystalline Powder, Crystals or Platelets

Density：

1.2±0.1 g/cm3

Melting Point：

73 °C

Boiling Point：

108 °C12 mm Hg(lit.)

Flash Point：

86.1±18.7 °C

Refractive Index：

1.435

Water Solubility：

H2O: soluble

Storage Conditions：

Store below +30°C.

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

2811

wgk germany：

hazard class code：

36/37/38-48-23/25-25

safety instructions：

26-37/39-45-38-36/37/39-22-36/37

Marks：

Xi,T

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Danger|H301 (53.57%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 84 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

methyl carbazate

Methyl carbazate Use and Manufacturing

Methods of Manufacturing

A mixture of dimethyl carbonate (1, 45.0 g, 0.50 mol) and hydrazine hydrate (29.4 mL, 0.48 mol) was added into a 250 mL round-bottom flask equipped with a condenser. The reaction mixture was heated to 50 °C, stirred for 30 min, and then stirred at room temperature for 24 h. Water, methanol, and excess dimethyl carbonate were distilled off under reduced pressure. After dryness, a white crystal (2) (42.3 g) was obtained with a yield of 94percent, mp 69-70 °C.A mixture of dimethyl carbonate (1, 45.0 g, 0.50 mol) and hydrazine hydrate (29.4 mL, 0.48 mol) was added into a 250 mL round-bottom flask equipped with a condenser. The reaction mixture was heated to 50 °C, stirred for 30 min, and then stirred at room temperature for 24 h. Water, methanol, and excess dimethyl carbonate were distilled off under reduced pressure. After dryness, a white crystal (2) (42.3 g) was obtained with a yield of 94percent, mp 69-70 °C. 1H NMR (300 MHz, CDCl3): δ 3.73 (s, 3H, CH3 -O), 3.77 (d, 2H, J=1.85 Hz, -NH2), 6.09 (s, 1H, -NH).Hydrazine hydrate (80percent, 188 mL, 3 mol) was added dropwise to a solution of dimethyl carbonate (281 mL, 3.3 mol) over 1 h at 50 °C. On the completion of addition, the mixture was stirred at 70 °C for 4 h. Then the mixture was cooled to 0 °C. The precipitate was collected by filtration, washed with petroleum ether and dried to give compound 3 as a white solid; yield 246 g (91percent); m.p. 68–69 °C (lit.29 69–70 °C); 1H NMR (600 MHz, CDCl3): δ 6.10 (br, 1H), 3.77–3.73 (m, 5H).In a 25 mL two-necked flask, 3 mL (35.6 mmol) of dimethyl carbonate and 0.85 mL (17.5 mmol) of hydrazine hydrate (80percent) were added, 0.2 g of zinc powder was added as a catalyst, Heated to reflux 5h, hot filtered to remove zinc powder, Excess dimethyl carbonate was distilled off at atmospheric pressure, the remaining liquid was cooled with cold water to stand, needle crystallization precipitated, dried to give a white solid 1.11g, a yield of 70.6percent.

Uses

Hydrazine derivative.

Manufacturing Info：

Hydrazinecarboxylic acid, methyl ester: ACTIVE

Computed Properties

Molecular Weight:90.08
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:90.042927438
Monoisotopic Mass:90.042927438
Topological Polar Surface Area:64.4
Heavy Atom Count:6
Complexity:53.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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