1-Boc-hexahydro-1,4-diazepine Property

Melting point:

143.4 °C

Boiling point:

95-110 °C0.5 mm Hg(lit.)

Density 

1.016 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.471(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.45±0.20(Predicted)

form 

Liquid

Specific Gravity

1.016

color 

Colorless to yellow

Water Solubility 

Not miscible or difficult to mix in water.

Sensitive 

Air Sensitive

BRN 

7581789

CAS DataBase Reference

112275-50-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2735

WGK Germany 

3

F 

10-34

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HazardClass 

8

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Boc-hexahydro-1,4-diazepine Chemical Properties,Usage,Production

Chemical Properties

Colorless to yellow liquid

Uses

1-Boc-hexahydro-1,4-diazepine is a diazepine derivative used in the preparation of pharmaceutical compounds such as histamine H3-receptor antagonists and dipeptidyl peptidase IV (DPP-IV) inhibitors.

Uses

1-Boc-homopiperazine is used in synthesis of potent anticoagulant. It is also used to produce 4-(7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester by reaction with 11-bromo-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline.

General Description

1-Boc-hexahydro-1,4-diazepine is an N-boc protected homopiperazine. Its enthalpy of vaporization at boiling point (558.15K) is 49.498kjoule/mol.

Synthesis

To a solution of di-tert-butyldicarbonate (2.201 g, 9.780 mmol) in acetic acid (9.8 mL), a solution of 1,4-diazepane (1.0 g, 9.780 mmol) in acetic acid (9.8 mL) is added at room temperature. After 24 hours, water is added and the pH is adjusted to 10 using 10% NaOH. The aqueous phase is then extracted with dichloromethane (2 x 15 mL). The organic phase is dried and the solvent is evaporated to obtain tert-butyl 1,4-diazepane-1-carboxylate (1-Boc-hexahydro-1,4-diazepine) with a yield of 90.0%.

Precautions

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. It is sensitive to air.

References

Synthesis and biological activity of novel 1,4-diazepane derivatives as factor Xa inhibitor with potent anticoagulant and antithrombotic activity. Bioorganic &Medicinal Chemistry. 2004, 12 (9), 2179-2191.
Discovery and structure-activity relationship of thienopyridine derivatives as bone anabolic agents. Bioorganic & medicinal chemistry. 2013, 21 (7), 1628-1642.