| Identification | More | [Name]
1-Adamantaneacetic acid | [CAS]
4942-47-6 | [Synonyms]
1-ADAMANTANEACETIC ACID
1-ADAMANTYLACETIC ACID
1-CARBOXYMETHYLADAMANTANE
2-(1-ADAMANTYL)ACETIC ACID
ADAMANTYL ACETIC ACID
AKOS B019591
AKOS BBS-00006339
AKOS MSC-0706
CHEMBRDG-BB 4013929
IFLAB-BB F1928-0005
LABOTEST-BB LT00007833
RARECHEM AQ TC 1008
tricyclo[3.3.1.13,7]dec-1-ylacetic acid
Tricyclo[3.3.1.1(3,7)-]decane-1-acetic acid
1-carboymethyl adamantane
1-Adamantaneaceticacid,98+%
1-ADAMANTANEACETIC ACID 99+%
1-ADAMANTANEACETIC ACID PURUM 98%
1-ADAMANTANEACETIC ACID (1-ADAMANTYLACETIC ACID)
1-carbonylmethyladamantane | [EINECS(EC#)]
225-585-1 | [Molecular Formula]
C12H18O2 | [MDL Number]
MFCD00074728 | [Molecular Weight]
194.27 | [MOL File]
4942-47-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline powder or crystals | [Melting point ]
134-137 °C (lit.) | [Boiling point ]
270.73°C (rough estimate) | [density ]
1.0086 (rough estimate) | [refractive index ]
1.4949 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Solubility in Methanol - almost transparency | [form ]
Crystalline Powder or Crystals | [pka]
5.00±0.10(Predicted) | [color ]
White to off-white | [BRN ]
641412 | [InChI]
InChI=1S/C12H18O2/c13-11(14)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2,(H,13,14) | [InChIKey]
AOTQGWFNFTVXNQ-UHFFFAOYSA-N | [SMILES]
C12(CC(O)=O)CC3CC(CC(C3)C1)C2 | [CAS DataBase Reference]
4942-47-6(CAS DataBase Reference) | [NIST Chemistry Reference]
1-Adamantaneacetic acid(4942-47-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R15:Contact with water liberates extremely flammable gases.
R10:Flammable. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S7/8:Keep container tightly closed and dry . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29162090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white crystalline powder or crystals | [Uses]
1-Adamantaneacetic acid was used as an acylating agent in determining pharmacological characteristics of ten new analogues of bradykinin (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg) that were modified in the N-terminal part of the molecule. | [Biochem/physiol Actions]
1-Adamantaneacetic acid is an inhibitor of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232). | [Synthesis]
General procedure for synthesizing 1-adamantylacetic acid from methyl 2-(adamantan-1-yl)acetate and sodium bicarbonate: referring to the preparation of 2-adamantylacetic acid in Example 10, 2.53 g of sodium hydroxide was dissolved in 433 mL of methanol, and 1,125 mL of methanol solution containing 150 g (0.72 mol) of methyl 2-adamantylacetic acid was added, and the reaction was stirred at room temperature for 6 hours at room temperature with stirring. Upon completion of the reaction, the reaction mixture was concentrated under vacuum. To the concentrated residue was added aqueous sodium bicarbonate solution and the mixture was washed with ether. Subsequently, the aqueous layer was adjusted to pH 1 with 12N hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated in vacuum to give the target product 1-adamantaneacetic acid. Yield: 129.39 g, 93% yield. | [Purification Methods]
Dissolve the acid in hot NaOH, treat with charcoal, filter and acidify. Collect the solid, wash it with H2O, dry and recrystallise it from
MeOH. [Stetter et al. Chem Ber 92 1629 1959.] The acid chloride [2094-72-6] has M 168.7, m 51-54o,
and b 135-136o/1mm. LACHRYMATORY. | [References]
[1] Patent: US5658923, 1997, A |
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