tert-Butyl carbazate Chemical Properties

Melting point:

39-42 °C (lit.)

Boiling point:

63-65 °C/0.1 mmHg (lit.)

Density 

1.02

refractive index 

1.4496 (estimate)

Flash point:

197 °F

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in ethanol and methanol.

pka

10.74±0.20(Predicted)

form 

Crystalline Lumps

color 

White to slightly yellow

Sensitive 

Moisture Sensitive

BRN 

1756967

InChIKey

DKACXUFSLUYRFU-UHFFFAOYSA-N

CAS DataBase Reference

870-46-2(CAS DataBase Reference)

EPA Substance Registry System

Hydrazinecarboxylic acid, 1,1-dimethylethyl ester (870-46-2)

Safety Information

Hazard Codes 

T-F,T,F

Risk Statements 

48-36/37/38-24/25-11

Safety Statements 

45-36/37/39-16-24/25

RIDADR 

1325

WGK Germany 

3

F 

21

TSCA 

Yes

HazardClass 

4.1

PackingGroup 

III

HS Code 

29280090

MSDS

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tert-Butyl carbazate Usage And Synthesis

Chemical Properties

White to pale yellow lumps

Uses

Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection.

Uses

tert-Butyl carbazate is used in a palladium-catalyzed cross-coupling with vinyl halides to prepare N-Boc-N-alkenylhydrazines. It is utilized in solid phase peptide synthesis and in the optical purity determination of alfa-amino aldehyde. It reacts with aldehydes to get hydrazones, which finds application as an intermediate in the synthesis of HIV-1 protease inhibitors. In addition to this, it is used as a starting material for the preparation of BOC-azide, sulfonic and carboxylic hydrazides.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2725, 1960 DOI: 10.1021/ja01496a018
Chemical and Pharmaceutical Bulletin, 18, p. 217, 1970 DOI: 10.1248/cpb.18.217

Purification Methods

Distil it in a Claisen flask with a water or oil bath at ca 80o. After a couple of drops have distilled, the carbazate is collected as an oil which solidifies to a snow white solid. It can be crystallised with 90% recovery from a 1:1 mixture of pet ether (b 30-60o) and pet ether (b 60-70o). [Carpino et al. Org Synth Coll Vol V 166 1973, Caprino et al. Org Synth 44 20 1964, Beilstein 3 IV 175.]

tert-Butyl carbazate(870-46-2)Related Product Information

• butyl rubber
• Buprofezin
• Methyl 4-tert-butylbenzoate
• Di-tert-butyl dicarbonate
• Butyl benzoate
• tert-Butyldimethylsilyl chloride
• tert-Butanol
• TEREPHTHALIC DIHYDRAZIDE
• tert-Butyl methyl ether
• Di-tert-butyl peroxide
• 4-tert-Butylphenol
• Cyhalofop-butyl
• Isobutyl chloroformate
• Butyl methacrylate
• 4-tert-Butylcatechol
• Diisobutyl phthalate
• tert-Butyl acetate
• tert-Butyl peroxybenzoate