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2094-72-6

Basic Information
CAS No.: 2094-72-6
Name: 1-Adamantanecarbonyl chloride
Article Data: 27
Molecular Structure:
Molecular Structure of 2094-72-6 (1-Adamantanecarbonyl chloride)
Formula: C11H15ClO
Molecular Weight: 198.692
Synonyms: 1-Adamantanecarbonylchloride (6CI,7CI,8CI);1-Adamantanecarboxylic acid chloride;1-Adamantanoylchloride;1-Adamantoyl chloride;1-Adamantylcarbonyl chloride;1-Adamantylcarboxylic acid chloride;NSC 179368;NSC 249324;
EINECS: 218-252-7
Density: 1.239 g/cm3
Melting Point: 49-51 °C(lit.)
Boiling Point: 270.6 °C at 760 mmHg
Flash Point: 139 °C
Solubility: may decompose with water
Appearance: white to almost white crystalline solid
Hazard Symbols: CorrosiveC
Risk Codes: 14-34-37
Safety: 26-36/37/39-45-24/25
Transport Information: UN 3261 8/PG 2
PSA: 17.07000
LogP: 2.96820
Synthetic route
828-51-3

1-Adamantanecarboxylic acid

2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
With thionyl chloride at 80℃; for 2h;100%
With oxalyl dichloride; N,N-dimethyl-formamide at 25℃; for 1.5h;100%
With thionyl chloride at 80℃; for 3h;99%
768-90-1

1-Adamantyl bromide

2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) magnesium, 1,2-dibromoethane / 1.) diethyl ether, 35 deg C
2: 90 percent / SOCl2 / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / hexane / 5 h / Cooling with ice
2: thionyl chloride / benzene / 5 h / 80 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium; iodine / diethyl ether / 2 h / Inert atmosphere
1.2: 3.5 h / Inert atmosphere
2.1: thionyl chloride / 1 h / 80 °C
View Scheme
104164-53-6

adamantoyltris(trimethylsilyl)germane

A

104164-55-8

tris(trimethylsilyl)germyl chloride

B

{(CH3)3Si}2Ge{C(OSi(CH3)3)C10H15}

C

67-66-3

chloroform

D

2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
In tetrachloromethane byproducts: Me3SiCl, hexachloroethane; Irradiation (UV/VIS); NMR tubes contg. the acylgermane/CCl4 sealed under vac., irradiated (two 100W Hg lamps, λ>360 nm) for up to 3h, with cooling to -15°C), soln. remained colourless; not isolated, detected by NMR-spect.;A >65
B 0%
C <1
D >99
281-23-2

adamantane

2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine / 6 h / 85 °C
2.1: magnesium; iodine / diethyl ether / 2 h / Inert atmosphere
2.2: 3.5 h / Inert atmosphere
3.1: thionyl chloride / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine / 85 - 110 °C
2: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C
3: thionyl chloride / 2 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine / 85 - 110 °C / Green chemistry
2: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C / Green chemistry
3: thionyl chloride / 2 h / 80 °C / Green chemistry
View Scheme
117-10-2

1,8-dihydroxy-9,10-anthracenedione

2094-72-6

1-Adamantanecarbonyl chloride

C36H36O6

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
81250-34-2

1,3-dipropyl-5,6-diaminouracil

2094-72-6

1-Adamantanecarbonyl chloride

144-55-8

sodium hydrogencarbonate

127946-26-3

1,3-dipropyl-8-(1-adamantyl)xanthine

Conditions
ConditionsYield
In pyridine100%
911010-77-0

7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

2094-72-6

1-Adamantanecarbonyl chloride

911006-44-5

C25H30N4O

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 160℃; for 0.116667h; Product distribution / selectivity; Microwave irradiation;100%
6346-09-4

4-aminobutyrylaldehyde diethylacetal

2094-72-6

1-Adamantanecarbonyl chloride

1148156-24-4

N-(4,4-diethoxybutyl)adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

2094-72-6

1-Adamantanecarbonyl chloride

(S)-2-adamantanecarbonyloxy-2'-hydroxy-1,1'-binaphthyl

Conditions
ConditionsYield
With triethylamine In dichloromethane at -10 - 20℃;100%
With dmap; triethylamine In tetrahydrofuran at -5 - 20℃; for 24h; Inert atmosphere;95%
With dmap; triethylamine In tetrahydrofuran at -10 - 20℃; Inert atmosphere;95%
771-99-3

4-phenylpiperidine

2094-72-6

1-Adamantanecarbonyl chloride

312504-53-3

C22H29NO

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 0.5h;100%
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Chemistry

Molecular structure of 1-Adamantanecarbonyl chloride (CAS NO.2094-72-6) is:

Product Name: 1-Adamantanecarbonyl chloride
CAS Registry Number: 2094-72-6
IUPAC Name: Adamantane-1-carbonyl chloride
Molecular Weight: 198.6892 [g/mol]
Molecular Formula: C11H15ClO
XLogP3: 3.6
H-Bond Donor: 0
H-Bond Acceptor: 1 
EINECS: 218-252-7
Melting Point: 49-51 °C(lit.)
Surface Tension: 45.4 dyne/cm
Density: 1.239 g/cm3
Flash Point: 139 °C
Enthalpy of Vaporization: 50.88 kJ/mol
Boiling Point: 270.6 °C at 760 mmHg
Vapour Pressure: 0.00678 mmHg at 25°C
Storage temp.: 2-8°C
Water Solubility: may decompose with water
Sensitive: Moisture Sensitive
Product Categories: Adamantane derivatives;Adamantanes;Acid Halides;Carbonyl Compounds;Organic Building Blocks

Safety Profile

Safty information about 1-Adamantanecarbonyl chloride (CAS NO.2094-72-6) is:
Hazard Codes: CorrosiveC
Risk Statements: 14-34-37 
R14 :Reacts violently with water. 
R34:Causes burns. 
R37:Irritating to respiratory system
Safety Statements: 26-36/37/39-45-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S24/25:Avoid contact with skin and eyes.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
F: 10-21
HazardClass: 8
PackingGroup: III

Specification

 1-Adamantanecarbonyl chloride , its cas register number is 2094-72-6. It also can be called Tricyclo(3.3.1.1'3,7)decane-1-carbonyl chloride ; Adamantoyl chloride .It is a white to almost white crystalline solid.

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